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Synthesis of Aliphatic Sulfur Pentafluorides by Oxidation of SF5-Containing Anisole, Phenols, and Anilines

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F14%3A00433492" target="_blank" >RIV/61388963:_____/14:00433492 - isvavai.cz</a>

  • Result on the web

    <a href="http://dx.doi.org/10.1021/jo501562z" target="_blank" >http://dx.doi.org/10.1021/jo501562z</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/jo501562z" target="_blank" >10.1021/jo501562z</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Synthesis of Aliphatic Sulfur Pentafluorides by Oxidation of SF5-Containing Anisole, Phenols, and Anilines

  • Original language description

    4-(Pentafluorosulfanyl)catechol, 2-amino-4-(pentafluorosulfanyl)phenol, and 2-amino-5-(pentafluorosulfanyl)phenol undergo oxidation by lead tetraacetate at ambient temperature leading to dearomatization and the formation of SF5-substituted nitrites and esters of cis,cis-hexa-2,4-dienedioic (muconic) acid in good yields. 4-(Pentafluorosulfanyl)phenol and 4-(pentafluorosulfanyl)anisole are oxidized by 3096 aqueous hydrogen peroxide in concentrated sulfuric acid to provide 2-(5-oxo-3-(pentafluorosulfanyl)-2,5-dihydrofuran-2-yl)acetic acid [3-(pentafluorosulfanyl)muconolactone] and small amounts of side products-SF5-containing maleic and succinic acids. The methods presented are the first examples of the practical synthesis of aliphatic SF5-containing compounds from readily available aromatic ones.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

    <a href="/en/project/GAP207%2F12%2F0072" target="_blank" >GAP207/12/0072: Development of new methodologies towards (pentafluorosulfanyl)benzenes.</a><br>

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2014

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Journal of Organic Chemistry

  • ISSN

    0022-3263

  • e-ISSN

  • Volume of the periodical

    79

  • Issue of the periodical within the volume

    18

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    6

  • Pages from-to

    8906-8911

  • UT code for WoS article

    000342121100047

  • EID of the result in the Scopus database